Uploading a .gif appears to be working correctly for me. Below are a couple possible causes. If none of these are at fault we can proceed with troubleshooting your issue. What is the size of the image you are trying to load? There is a 5MB limit to the size you can upload. If you have a lot of images uploaded you might be using up your memory allocation. If you go to: <a href="https://app.roll20.net/account" rel="nofollow">https://app.roll20.net/account</a> you can view your current memory usage (right hand side of the page). Please let me know if either of these help. If they do not we can work further to resolve the problem. - Gauss